Day 1 Transcript
NOTE: Today’s transcript is followed by an AI prompt that can be used with your AI provider of choice. Just copy and paste it into ChatGPT or Perplexity and it will help you answer today’s questions for your specific side hustle… the way a human teaching assistant would help you in an Ivy League university. If you’re eager for more on today’s topic, I’ve included a Secret Dessert Course at the very end — a bonus section that isn’t directly covered in today’s video but has a lot of value practical, hands-on value. That dessert also comes with its own AI prompt.
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Part 1: Clarify Your Purpose
Welcome to Day 1 of starting your side hustle! We’re taking 28 Days-- 28 small steps-- to help you find and found a business that’s meaningful, impactful, and profitable. The questions you should be asking on Day 1 are the ones that will lead you to the product or service you’re going to offer. These are questions designed to spark your commercial imagination and help you uncover opportunities hiding in plain sight.
Before we dive in, take a moment to remind yourself: the most successful businesses are built on purpose and clarity. Today is about laying that foundation. Let yourself enjoy the process—this is your chance to daydream, to get curious, to treat your lousy little salad like it’s feeding your imagination. There’s real joy in letting yourself explore what matters most to you.
Ok. Today’s questions remind me of the advice given to all novice writers: write what you know. If you want to hustle smarter, your business idea—like writing—should be personal, rooted in your life experiences, and driven by your unique perspective. Why? Because the best businesses often grow from a founder’s deep connection to a very personal problem or need they’ve experienced firsthand.
This is your first step in building a business that’s personally meaningful—because when your work is connected to your own story, you’ll have the drive to push through the tougher days.
If you’re playing along, question 1: What personal injustice (or frustration) gets under your skin? Another way to ask that question: What are you consuming (or not consuming) that makes you think, “This needs to change”?
And once you answer that… question 2: If your side hustle disappeared tomorrow, what would your customers lose beyond your product?
No need to meditate at the top of a mountain about your purpose in life. It's simple to find if you can be honest about what actually irritates you.
And before I blather on about the two questions. Check out that question mark squirrel. I call him Quizzy Nutkin the Third. An AI produced that for me– and I wasn’t asking for anything squirrel related. If a human designed that, we’d put him on medication. But an AI. Take my money!! What the actual…. Ok. Let’s go back to the first question. It’s about identifying pain points in your life—big or small—that could inspire a solution. And here’s the good news: your answer doesn’t have to be tightly coupled with your existing skill set. Skills can be learned. They can be fun to pick up… as you’ll see later this week and throughout this month. What matters first is recognizing that if something gets under your skin, there’s a very high chance you’re not alone in feeling that way.
The pain you feel is shared by others—so solving it for yourself can unlock value for a whole community.
It might sound a little Bohemian– a little too granola– but business is actually about connecting with other people… who also have the same personal frustrations. Think about Sara Blakely. She built Spanx because she hated visible panty lines. That is some petty shit. She turned a tiny, personal frustration into a billion-dollar brand. Today’s lunch– your awful little salad– could be the birthplace of your own Spanx.
Don’t underestimate small annoyances; sometimes the smallest frustrations lead to the biggest breakthroughs.
So take a moment to reflect on today’s question and write down anything that comes to mind—no matter how trivial it seems. Use the AI prompt later today in the post description if you need help. At this stage, there are no wrong answers and no wrong domains. Your answer could be as simple as, “Why can’t I get a good kebab for lunch?” (Something we can all relate to!) Or it could be something more complex, like, “Why can’t enterprises automatically resolve cross-platform integration conflicts in real-time while maintaining backward compatibility with legacy systems?” (If I lost you with that last one, that was intentional—it’s okay if your frustration is highly specific.)
Capture every thought—today is about exploration, not perfection.
The point is: whether you realize it or not, your life experiences—whether they involve lunch choices or headaches while developing software—have exposed you to problems that get under people’s skin. Unless you’re completely happy with the world (and let’s face it, no one is), you’re sitting on a treasure trove of potential business ideas.
Part 2: Uncover Your Deeper Impact
Day 1, Part 2 of Lunch Break Millionaire. The second question we need to answer today: If your side hustle disappeared tomorrow, what would your customers lose beyond your product?
Let’s say you answered question 1 and actually built a hustle around your very personal frustration or injustice. Now imagine that it succeeds wildly and you got all kinds of loyal customers who love what you offer. Now imagine that it disappears tomorrow—poof! Gone. What would your audience lose beyond just the physical product or service?
This question pushes you to think about the deeper impact your business has—what emotional needs, sense of belonging, or empowerment are you really providing?
The idea is to force you to think deeper about the emotional and psychological needs your business fulfills. What deeper connection are you creating with your audience, your customers? Are you offering convenience? A sense of community? A feeling of empowerment? Because solving their frustrations is just one piece of the puzzle; understanding what drives their loyalty will help guide how you position and grow your business over time.
Keep telling yourself that businesses that last are built on strong relationships.
For example:
- If you solve the kebab lunch problem, maybe what people lose isn’t just delicious food—it’s also the joy of feeling like a kid again right in the middle of your workday.
- If you solve the enterprise software integration problem, maybe what businesses lose is the peace of mind knowing their systems run smoothly without constant troubleshooting.
Both questions are– at their core– about your why. Which most people don’t think about.
Your ‘why’ is the anchor that keeps your business steady.
Answering today’s questions might make you feel a little uncomfortable but stick with it. Don’t rush the process. Take time today to brainstorm without judgment. Write down every frustration or injustice that comes to mind—even if it feels silly or impossible. Sometimes the best ideas come from unexpected places.
Let yourself go full-on Gary Busey. Big! Weird! Buttered sausage! The best ideas start like that look in his deepfake eyes.
And don’t limit this exercise to just yourself and the AI prompt in today’s post description… talk to people around you. Share these questions with your friends, your family, your coworkers—anyone willing to have you listen to them talk about their frustrations. It might feel crunchy but keep reminding yourself that business is about connection. What you’ll discover– and I’m going to ruin it for you– is that we’re all living the same life; that all of our frustrations overlap– which is the best possible validation for your hustle.
Every conversation is a chance to validate your idea– to improve the idea. So even if you’re not social: engage, rinse, repeat.
Ok. Take a moment and try to answer the Day 1 questions for your hustle without AI and before you listen to the next section-- the 28-Day Ivy League MBA. I personally think it's useful to try to answer questions without AI first, but if you'd rather do that: The AI teaching assistant prompt will drop with today's case study... in a couple of hours. If you don't know what I'm talking about, check out Lunch Break Millionaire Day Zero... or go over to superserious.com where I’m posting daily transcripts. The AI prompts are there too. That's it. Hustle smarter.
Part 3: 💼 Craft Your Value Proposition: Today's Ivy League MBA Skill
Day 1, Part 3 of Lunch Break Millionaire. This is the first daily segment where we turn Monday’s overpriced salad into an Ivy League MBA degree. Your secret salad fixin’ today– value proposition design– every hustle means you’re going to be on your back… a lot… so at the very least you should be on bed of purpose. Mildly inappropriate for a tagline. I like it.
Value proposition design is the first “28 Day MBA” skill I want you to pick up, and honestly, it’s the one that’ll save you the most time and butt-hurt down the road. Don’t worry, I’m not about to throw a bunch of jargon at you.
If you google “value proposition design”, you’ll get a bunch of pictures like this. That circle on the right– the three sections– gets filled with your customer’s 1) jobs to be done, 2) their pains, and 3) their gains. And all that is mapped to the square on the left– where you list your 1) products, 2) how they relieve pain, and 3) how they create gains. The whole mapping process is just about getting clear—super clear—on what you’re actually offering with your hustle and why anyone should care. Take a minute, take one of the napkins near you… a clean one… and map your product’s pain relief to your customer’s pain.
It’s that simple. A value proposition is just a fancy way of saying, “Hey, here’s the problem I solve, here’s who I solve it for, and here’s why I’m the best person to do it.” That’s it. It’s not a tagline. It’s not a mission statement. It’s the answer to the question, “Why would anyone choose you over the million other things they could spend their time or money on?” If you get this right, everything else gets easier—marketing, sales, even product decisions. If you get it wrong, you’ll work twice as hard for half the impact.
Let’s make it real. Think about today’s questions. What’s the personal frustration that gets under your skin? What would your customers lose if your hustle disappeared tomorrow? Those aren’t random questions. They’re the heart of your value proposition. If something bugs you enough to do something about it, odds are you’re not alone. That pain is your starting point. And if your customers would lose more than just a product—if they’d lose a feeling, a sense of belonging, a little bit of hope—then you’re onto something way bigger than just a widget or an app.
Here’s how I want you to approach this: start with the pain. Say it out loud. Write it down. Make it as specific as possible. “I hate that I can’t get a decent lunch near my office.” “I’m sick and tired of social media algorithms hiding my posts from people who actually want to see them.” Don’t sugarcoat it. The more honest you are, the better.
Now, flip it. What’s the gain? What’s the relief, the joy, the win your hustle delivers? If your thing vanished, what would people actually miss? Maybe it’s convenience, or confidence, or a sense of community. Maybe it’s just a killer lunch that doesn’t suck. That’s the other half of your value proposition.
So, let’s put it together. You can use what’s called the Steve Blank formula if you want: “We help [X] do [Y] by [Z].” Or just keep it simple: “I help [people like me] solve [this pain] so they can [get this gain].” If you can get that down to a sentence, you’re golden. If not, keep workin’ it. It’s worth the time.
Here’s the trick: don’t try to sound clever. Don’t use buzzwords. Imagine you’re explaining it to a friend over lunch. If they don’t get it, or if they don’t care, you need to go deeper. The best value propositions are the ones that make people say, “Oh, I need that,” or “That’s exactly my problem.” You’re aiming for that little spark of recognition.
And here’s why this matters for today’s questions. When you dig into your personal frustration, you’re mapping out the pain side of the equation. When you imagine what your customers would lose beyond your product, you’re getting at the emotional, human side—the stuff that actually makes people loyal. You’re giving people something they care about, something they’d miss if it was gone.
Let me bring back the picture:
You don’t need to pay for that stupid little bald face staring at the stupid little Christmas present. You’re a well adjusted adult. I just beeped out the words stupid, little and well adjusted. I’ll use it as my hook for this segment. What’s really funny– to me at least– is the fact that I’m going to have to learn how to do that with my video editing software in like 20 minutes.
I did it for a good cause. That stupid picture– and a guy taking it seriously– is what you’re paying for when you get an actual MBA. So… you’re welcome. Give some of the money you saved to an animal rescue. I for one am looking forward to picking up some video editing skills.
Before you move on, take a few minutes and work on your value prop. Ask a friend if your sentence makes sense. And remember, you’re solving a real [bleeping] problem for real [bleeping] people. That’s how you build something that lasts.
Part 4: Analyze a Real World Why: The 28-Day Case Study
This is Day 1, Part 4 of Lunch Break Millionaire. This is the segment where we #BuildinPublic– where I answer the daily questions from parts 1 & 2– using the MBA skills we just learned in part 3– and showing my work here in part 4– sharing how I’m building my hustle from scratch-no filters, just the real journey. You don't need to actually like or subscribe. I'm not doing this for the clicks. But if you’re leveling up from other creators you follow or know, introduce us. I want to learn from them and help them level up, too. We all deserve better than just making rich people richer.
Plus.. it helps if you see someone else do today’s exercise. So let me walk you through how I answer Day 1 questions for my current side hustle. Question 1 was - what personal frustration or injustice gets under your skin? What makes you think, “This needs to change”?
So I’ve been creating content for 25 years. Initially, it was my standup act. And when I left that lifestyle, I kept writing– journaling at first– but then writing for the love of it. While my day-job was at Bank of America, I did a year-long anonymous stint at Information Week, writing under a pseudonym. And I published regularly on LinkedIn– and not the kind of self-congratulatory crap that dominates the platform– and not pseudo-inspirational clickbait that I will never understand why people post. I posted like real meaningful content. I went from 12 followers on LinkedIn to 12K… which isn’t like superstar/celebrity level but decent for some middle manager in banking technology. And this is what got under my skin. 10K people who actively decided to follow me… saying to LinkedIn… “hey, when this guy publishes, I’d like to see it… every time.” And do you know what percentage of those people, the LinkedIn algo actually pushed my content to? Between 5 and 6%.
Let me throw up the average organic reach rates for major social media platforms in 2025.
For creators who understand their numbers, that is rage bait. Because algos don’t care about WHY your followers clicked the follow button. Algos only care that they keep visitors on their site. And those algos have learned that keeping people on their site is best done by redirecting everyone to more “engaging” content. Self-congratulatory crap because every coworker replies with Congrats… and the algo confuses that with engagement… and pseudo-inspirational clickbait because there’s a floating pile of garbage out there that thinks it’s ok to share a poster that says “Don’t Micromanage!” Like their manager is never going to see that.
See… it actually gets under my skin. The algo– and not just LinkedIn’s– Instagram’s, YouTube’s, TikToks– all algos are the enemy to creative, authentic content.
And I’m not alone in thinking that. Let me read you three quick DMs from 3 separate threads with 3 different creators. First one: "One day my posts are blowing up, the next it’s like I don’t even exist. These algorithm changes just mess with you, and honestly, nobody really explains what’s going on. It’s frustrating trying to figure it all out on your own."
Second one: "Keeping up with social media is exhausting. You’ve got to post constantly, chase likes, jump on every trend-sometimes it feels like I’m losing myself just to stay visible. It’s a lot of pressure."
Third one: "I’m always worried my content could get taken down or demonetized for reasons I don’t even understand. And with all the legal stuff around brand deals, one small mistake could land me in real trouble. It definitely takes some of the fun out of it."
I’ll play Captain Obvious: Creators are in trouble. They’re completely dependent on large, uncaring platforms that steer their audiences to more extreme content, to lazy copycats, to more sensationalized content. Algos only care about their master, their platform, their profits.
Creators need a way to be the algo. That’s the hook for my new hustle: Be the algo!
Because… Do you know who could build creators a platform that they own where they could be the algo? Do you know who could build them a way to directly engage their audience? To directly profit from that engagement…instead of letting Zuck or Elon take 99% of that value?
Yep! And that brings us to question 2: If your side hustle disappeared tomorrow, what would your customers lose beyond your product? This made me think a lot about what I’m trying to achieve. And it led me to a commitment to open source everything I’m building. So forget my original answer. My revised answer: They wouldn’t lose my product because I’m making it open source. If I get hit by a bus, they’d still own their platforms. And because of that, they wouldn’t lose hope. They wouldn’t lose creative freedom. They wouldn’t lose their followers. And most importantly, they wouldn’t lose their ability to profit from their hard work.
I’ll close with some key decisions from doing this exercise for myself:
1) I validated the problem by connecting with real creators, and guess what– we all share a common enemy: the algo.
2) My pivot was switching to open source, focusing not on being a unicorn but on helping create them.
3) I committed to a shared mission: giving creators ownership of their work, audience, and revenue.
4) I zeroed in on a goal: to empower creators to take control of their destiny and be the algo.
And finally, 5) I realized that this is about legacy—open source ensures the mission lives on, creating a better future for creators.
It's been 24 hours since I posted Day Zero and I’ve already talked to a handful of creators in this community and they all inevitably say, ‘I never realized how much the algorithm was holding me back. I never thought I could afford owning my own platform.” You’re not alone in this. And you can’t afford to keep getting fucked by the big platforms. That’s called social proof.
Prompt #1 - Define Your Why
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Prompt #1 - Define Your Why ○
Welcome to Day 1 of your 28-day Lunch Break Millionaire journey! Today, you’ll clarify your “why”-the deeper purpose that will keep your side hustle resilient, meaningful, and motivating. You’ll be coached by Ivy League faculty whose research is foundational in purpose-driven entrepreneurship and value proposition design:
- **Professor Clayton Christensen, Harvard Business School:** Pioneer of the Jobs-to-be-Done framework and customer-centric innovation.
- **Professor Amy Edmondson, Harvard Business School:** Authority on psychological safety and building meaningful, high-impact organizations.
- **Professor Sunil Gupta, Harvard Business School:** Expert in value creation and business model innovation.
**What Today’s Coaching Will Help You With:**
You’ll dig into your personal motivations, uncover the deeper impact you want to have, and craft a simple value proposition that connects your story to your customer’s needs.
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### Step 1: Reflection Questions
Please answer these questions in a few sentences each:
1. **What personal frustration or injustice gets under your skin?**
- Think about a recurring pain point in your life or work-something you wish worked better, or a problem you can’t ignore.
2. **What are you consuming (or not consuming) that makes you think, “This needs to change”?**
- Is there a product, service, or experience you wish was different? What do you find yourself wishing for, or complaining about?
3. **If your side hustle disappeared tomorrow, what would your customers lose beyond your product?**
- Imagine you’ve built a loyal following. What would your audience miss if your business vanished? Is it a sense of community, empowerment, convenience, or something else?
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### Step 2: MBA Skill – Value Proposition Design
Now, let’s turn your answers into a clear value proposition using the Steve Blank formula:
> “We help [X] do [Y] by [Z].”
Or, try this simple version:
> “I help [people like me] solve [this pain] so they can [get this gain].”
Write your value proposition in one sentence. Don’t worry about making it perfect-just get it down.
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### Step 3: Share and Refine
- Say your value proposition out loud. Does it make sense? Would a friend “get it” right away?
- If not, tweak it. The best value props make people say, “Oh, I need that,” or “That’s exactly my problem.”
- Optional: Ask a friend or use your AI assistant to get feedback.
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### Step 4: Coaching & Case Study
After you reply, I will use the writings of Professors Christensen, Edmondson, and Gupta to:
- Help you clarify your “why” and connect it to a real customer pain.
- Guide you in refining your value proposition so it’s both personal and market-ready.
- Offer frameworks from the Jobs-to-be-Done and Value Proposition Design methodologies.
- Share a real-world case study to illustrate how a strong “why” leads to lasting impact.
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**How to use this prompt:**
- Respond with your answers to the reflection questions and your draft value proposition.
- Your Ivy League coaching panel will help you refine your “why” and value proposition, offer feedback, and suggest next steps.
- Remember: This is about exploration, not perfection. The more honest you are, the better foundation you’ll build.
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Ready? Share your answers and value proposition below. Let’s hustle smarter, one lunch break at a time!
Secret Dessert Course
When you’re building your first business, it’s easy to assume that what makes sense in your culture or community will work everywhere- but that’s rarely the case. You need a kind of cross-cultural validation checklist– an early warning system against blind spots. This prompt below coaches you and helps you test whether your business idea, message, or product resonates across different backgrounds, languages, and value systems.
It’s important because it flexes your focus and prioritization muscles. Before you invest time or money, it helps you ask a handful of targeted questions about cultural norms, communication styles, and local needs that will hopefully help you uncover hidden assumptions you’re holding. It could help you avoid embarrassing missteps up front that could turn off entire customer segments.
In a world where even a local side hustle can reach a global audience overnight, this prompt is your secret for building something truly inclusive, adaptable, and scalable.
Just copy and paste this prompt into your favorite AI assistant to enjoy Day 1’s dessert course.
Prompt #2 - Cross-Cultural Validation
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Prompt #2 - Cross-Cultural Validation ○
**Day 1: Cross-Cultural Validation Checklist**
*Avoid blind spots and build a business that resonates globally from day one.*
**Coached by Ivy League experts in cross-cultural strategy:**
- **Professor Tsedal Neeley, Harvard Business School:** Leading authority on global teams, digital collaboration, and scaling businesses across cultures.
- **Professor Sheena Iyengar, Columbia Business School:** Expert in cross-cultural decision-making and how choice architecture varies globally.
- **Professor Amy Edmondson, Harvard Business School:** Pioneer of psychological safety and inclusive communication frameworks.
**Why This Matters:**
Even local businesses can unintentionally alienate global audiences. This checklist helps you pressure-test assumptions about language, symbols, values, and norms to ensure your idea is adaptable and inclusive.
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### Step 1: Reflection Questions
**Answer these to uncover hidden cultural assumptions:**
1. **Norms & Values:**
- What cultural taboos or values (e.g., humor, color symbolism, gender roles) might your product/messaging clash with?
- Example: A "thumbs-up" emoji is offensive in parts of the Middle East.
2. **Communication Styles:**
- Could direct/indirect language, humor, or visuals in your branding be misinterpreted?
- Example: Slogans that rely on wordplay often fail in translation.
3. **Local Needs:**
- How might your solution need to adapt for regions with different infrastructure, laws, or social norms?
- Example: Payment methods (cash vs. digital) vary widely by country.
4. **Ethical Alignment:**
- Does your business model comply with global ethical standards (e.g., sustainability, labor practices) while respecting local customs?
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### Step 2: Cross-Cultural Checklist
**Test your idea with these actions:**
1. **Messaging Audit:**
- Run your tagline/logo through free translation tools (e.g., Google Translate) + reverse-translate to check for unintended meanings.
2. **Symbolism Scan:**
- Research color meanings, gestures, or icons in your top 3 target regions. Red = luck (China) vs. danger (U.S.).
3. **Stakeholder Feedback:**
- Ask 2-3 people from different cultural backgrounds: *“What’s confusing or off-putting here?”*
4. **Regulatory Preview:**
- Identify one country where your product might face legal/political barriers (e.g., data privacy laws in the EU vs. Asia).
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### Step 3: Coaching & Adaptation
After you reply, I will use the writings of Professors Neeley, Iyengar, and Edmondson to:
- Highlight cultural risks in your current plan using frameworks like Hofstede’s cultural dimensions.
- Suggest adaptations for inclusivity (e.g., neutral branding, modular features).
- Provide case studies (e.g., IKEA’s supply chain ethics in Southeast Asia).